Keep It 21-Hundred:
Questions You
Should Be Asking
Your Date

We’re no stranger to doing hard things, and having hard conversations is a part of getting the sh*t done and healing somewhere along the way. So we asked our friends–single, dating, married, divorced–to share questions they feel are most important to ask when getting to know someone, whether it’s day one or day one-hundred.

Here are 21 real a** questions we should ask our bae-to-be or bae-for-life to help bring us closer to understanding each other. We’re ever-changing, so revisit this list. Be honest. Extend grace.

1. What are your intentions when seeking a partner and entering a relationship?

2. How do you feel about your relationship with your mother and father?

3. What house chore would you never want to do and why?

4. Are you interested in the same sex?

5. What is your worst memory?

6. How do you resolve conflict?

7. What are your top five priorities?

8. How do you hold yourself accountable?

9. What is your morning/night routine?

10. How do you show yourself love?

11. What offenses might you commit but not tolerate? Answer in the reverse.

12. Are you willing to seek individual and collective therapy?

13. How do you make, multiply, and spend money?

14. What’s your greatest fear in a relationship?

15. What’s your idea of vacation or a day off?

16. What is your workstyle?

17. What is off limits in the bedroom and why?

18. Describe the dynamics of your ideal relationship.

19. What can we not joke about?

20. How do you feel about yourself?

21. What are your final wishes?